2-Brompyridin
-Bromopyridine · Pyridine,2-bromo- · 2-BROMOPYRIDINE FOR SYNTHESIS · -Bromoazine · 2-Brompyridin · 2-Bromopyridine · 2-bromo-pyridin · o-Bromopyridine
Identifikatoren & physikalische Daten
| CAS No. | 109-04-6 |
|---|---|
| Summenformel | C5H4BrN |
| Durchschnittliche Molmasse | 158 g/mol |
| Monoisotopische Masse | 156,95271123 g/mol |
| SMILES | Brc1ccccn1 |
| InChIKey | IMRWILPUOVGIMU-UHFFFAOYSA-N |
| PubChem CID | 7973 |
| ChEMBL | CHEMBL331374 |
| ChEBI | CHEBI:51574 |
| EC No. | 203-641-6 |
| DTXSID | DTXSID6051564 |
| Lokaler Name | 2-Brompyridin |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 12,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 56 |
| Stoffklassen | Nitrogen Compounds -> Pyridines |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | 1.42 |
| Dampfdruck | 1.0 [mmHg] |
| Physical Description | Colorless oily liquid[EPA - PPRTV] Pale yellow or colorless liquid[Alfa Aesar MSDS] |
| Schmelzpunkt | 193°C |
| Siedepunkt | 192-194 °C (lit.) |
| Dichte | 1.657 g/mL at 25 °C (lit.) |
| Brechungsindex | n20/D 1.572(lit.) |
| Flammpunkt | 130 °F |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Löslichkeit | 20g/lSlightly miscible with water. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | pK1: 0.71(+1) (25°C) |
| Farbe | Clear colorless to pale brown |
| BRN | 105789 |
| Henry-Konstante | 1.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielektrizitätskonstante | 24.02 |
| Stabilität | Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides. |
| InChI | 1S/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H |
| InChIKey | IMRWILPUOVGIMU-UHFFFAOYSA-N |
| SMILES | Brc1ccccn1 |
| LogP (Verteilungskoeffizient) | 1.42 |
| CAS Datenbank | 109-04-6(CAS DataBase Reference) |
| NIST chemische Informationen | Pyridine, 2-bromo-(109-04-6) |
| EPA chemische Informationen | Pyridine, 2-bromo- (109-04-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH226 (16.7%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 60 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Pyridine, 2-bromo-Status: Active Update: 16-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/186202-Bromopyridine: HSNO Approval: HSR006014 Approved with controls |
| Gefahrenübersicht | A skin and strong eye irritantToxic by ingestionHighly toxic by skin absorption[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Flam. Liq. 3 (16.7%) |
| Toxicity Data | LC50 (rat) < 200,000 mg/m3/1hr |
| EPA Provisional Peer-Reviewed Toxicity Values | 2-BromopyridinePDF Document2011 |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2929 6.1/PG 2 |
| Zollcode | 29333999 |
| RTECS-Nr. | US3850000 |
| R-Sätze (R) | 10-24/25-36/37/38-23/24/25-20/21/22 |
| Gefahrensymbole | T,Xn,F |
| hazard_note | Toxic |
| Sicherheitshinweise (S) | 16-36/37-45-38-36/37/39-28A-26 |
| Gefahrenklasse | 6.1Acute Tox. 2 DermalAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
Anwendungen & Verwendung
Verwenden
2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist.
Herstellung & Synthese
synthetische
2-Bromopyridine is synthesized from 2-aminopyridine by bromination. In industrial production, hydrobromic acid (over 48%) is first cooled to below 0°C, 2-aminopyridine is slowly added, and then liquid bromine is added dropwise in a salt bath under freezing, and the rate of addition is to control the reaction temperature below -5°C appropriate. After adding, add sodium nitrite aqueous solution dropwise, control the reaction temperature to be below 0°C, stir for 20-30min, dropwise add 50% sodium hydroxide solution, extract the reaction solution with ether, wash with water, dry with anhydrous sodium sulfate, filter, and recover Diethyl ether, the residue was distilled under reduced pressure, and the 88°C-94°C/3333Pa fraction was collected to obtain the finished product of 2-bromopyridine with a yield of 83.8%.